Field Notes

On Asking Great Questions

At a recent board discussion focused on selecting a new CEO, one director asked an interesting question that sparked some deep thought and discussion. When comparing the experience of two candidates for the role, this director asked, “Is it 18 years’ experience or is it really 5 years’ experience over 18 years?” The conversation that ensued examined the nature of experience and the diminishing (even negative) returns after the same repetitive challenges in a job. The question posed moved the group to a trajectory no one could have anticipated and possibly shifted the focus on what criteria the board would rely on to assess its candidate choice.

Not all questions are that powerful, but the idea of asking a question rather than making a statement is central to effective leadership.

Leading through questions, as opposed to answers, has drawn considerable attention in the last few years for good reason. Extraordinary leaders know the power of dialogue in building consensus and solidifying trust. Leading through questions produces less resistance and engages people in a way no other message can. Questions strike a collaborative tone, even when the message is critical (Why do you think the project failed?). Questions suggest patience and a willingness to consider other views. When it comes to leadership, pound-for-pound questions out box answers and declaratives in just about any situation.

Because any content can be expressed as a question, leaders who want to carry a message that builds relationships often use questions as their vessel. Asking good questions is all about genuine curiosity and exploration and most of us just need the desire to ask them. A commitment to ask more questions and to carry more content through queries will improve any leader’s effectiveness.

When studying the best of leaders, we often stumble across a question that is beyond good or provocative. Some questions count as “great” in the effect they have on the conversation in which they occur. Great questions redirect focus and energy in a way nothing else can. So, let’s explore what constitutes a great question.

‎While any question can be “great” if it forges a new path forward, we suggest the best questions have some common elements.

  1. Great questions rarely have a correct answer.
  2. Great questions mine the deep meanings and assumptions we hold about an issue.
  3. Great questions propel a conversation in an unpredictable way.
  4. Great questions involve the parties to engage in deep inquiry together, rather than advocacy.
  5. Great questions always produce more questions.

Of those 5 criteria, it is the last one that is most reflective of “greatness.” We can always recognize a great question by how many other questions it generates. Great questions always give birth to more questions. That’s what makes them “great.” They move us forward not through answers but through other questions.

As Theodor Geisel (Dr. Suess) reminded us, “sometimes the answers are simple and the questions are hard.”

No one is born with great questions in their minds, but with practice and the desire to ask them, we can compose more great questions that add insight to the complexities we face every day. Great leaders ask great questions.

– RS

Begin Your Journey to Becoming a Better Leader

By purchasing the complete Admired Leadership® course, you’ll receive one year of full access to:

  • 15+ hours of video and audio content.
  • 100 behaviors, each explained in about 10 minutes or less.
  • Extensive study materials including behavior maps, questions, examples, and exercises.

In addition to the content, subscribers will receive access to the following:

  • Invitation to the annual Admired Leadership Community Conference.
  • Frequent live ALD Direct question and answer sessions with top executive advisors.
  • Weekly book summaries (like this one!) to stay abreast of the current writings on leadership.
  • Monthly study groups where leaders like yourself meet to discuss the Admired Leadership behaviors. An Admired Leadership coach will be on hand to facilitate the dialogue.